Ethyl Acetate → HCID 44225694, compound

HRID 1919280Notes

Reaction equation

HRID 1919280 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([OH:9])[C:6]([CH3:10])=[CH:5][C:3]=1[NH2:4].[H-].[Na+].[C:13]([C:17]1[N:21]=[C:20](Cl)[S:19][N:18]=1)([CH3:16])([CH3:15])[CH3:14].C(OCC)(=O)C>CN(C)C=O>[C:13]([C:17]1[N:21]=[C:20]([O:9][C:7]2[C:6]([CH3:10])=[CH:5][C:3]([NH2:4])=[C:2]([CH3:1])[CH:8]=2)[S:19][N:18]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 765444-Amino-2,5-dimethylphenolHCID 13193083HCID 13193083, compound

Product 1

HCID 44225694HCID 44225694, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

754 mg (5.50 mmol) of 2,5-dimethyl-4-hydroxyaniline are dissolved in 5 ml of N,N-dimethylformamide and slowly treated with 242 mg (6.05 mmol) of sodium hydride. The reaction mixture is stirred for 15 min, before 972 mg (5.50 mmol) of 3-(tert-butyl)-5-chloro-1,2,4-thiadiazole are added. Subsequently, the reaction mixture is heated at 100° C. for 1 h and then cooled down to AT. After addition of 20 ml of ethyl acetate, the solution is extracted three times with water and dried over MgSO4, and the solvent is removed under vacuum (1.46 g, 94% purity, 90% yield, log P (pH 2.3)=3.29).

Workup

  1. additionare added
  2. temperaturecooled down to AT
  3. extractionthe solution is extracted three times with water
  4. dry with materialdried over MgSO4
  5. customthe solvent is removed under vacuum (1.46 g, 94% purity, 90% yield, log P (pH 2.3)=3.29)

Sources & evidence

ORD record
ord-8b9092541a694e2f9f336c2762e30246
Source dataset
uspto-grants-2012_05
Patent number
US08168567B2

Reaction notes

Loading…